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β-Lapachone (CAS 4707-32-8)

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Synonym:3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione; ARQ 501; NSC 26326; NSC 629749; SL 11001
Application:A novel Topo I inhibitor
CAS Number:4707-32-8
Purity:98%
Molecular Weight:242.27
Molecular Formula:C15H14O3
Refer to Certificate of Analysis for lot specific data (including water content).
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Product NameCatalog #UnitPriceQtyAddFavorites
β-Lapachone sc-200875 5 mg $70
β-Lapachone sc-200875A 25 mg $295
Description
β-Lapachone, a novel Topo I (topoisomerase I) inhibitor, does not stabilize the cleavable complex indicating a novel mode of action, unlike camptothecin (sc-200871). Apoptosis has been demonstrated in HL-60 and human prostate cancer cells treated with β-Lapachone via a p53-independent mechanism and cell cycle arrest at G0/G1,2. β-Lapachone has been observed to accelerate wound healing by increasing cell proliferation in cells such as: keratinocytes, fibroblasts and endothelial while also increasing the migration of fibroblasts and endothelial cells. β-Lapachone has exhibited anti-inflammatory properties by suppressing the NF-κB activation by blocking IκBα degradation and downregulating the ERK, p38 mitogen-activated protein kinase and Akt pathway.
Usage
Store, as supplied, at room temperature for up to 1 year. Store solutions at - 20°C for up to 3 months.
Technical Information
Physical State:Solid
Derived from:Synthetic
Solubility:Soluble in DMSO (>25 mg/ml) at 5 °C, ethanol (20 mg/ml), chloroform, and DMF.
Storage:Store at room temperature
Melting Point:151-153 °C
Boiling Point:381.4 °C at 760 mmHg
Density:1.25 g/cm3
Refractive Index:n20D 1.60
Optical Activity:α20/D -43.9º, c = 2 in water
IC50:HIV-1 LTR: IC50 = 0.3 µM (human); HOS: IC50 = 1400 nM (human); MDA-MB-435 : IC50 = 0.06 ug.mL-1 (human); HL-60: IC50 = 1650 nM (human)
Ki Data:Lysine-specific demethylase : Ki= 3550 nM
Safety and Reference Information
WGK Germany:3
RTECS:QL6127400
PubChem CID:3885
MDL Number:MFCD01712233
Beilstein Registry:0181499
SMILES:CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
1. Li, C.J., et al. 1993. J. Biol. Chem. 268: 22463-22468. PMID: 8226754
2. Planchon, S.M., et al. 1995. Cancer Res. 55: 3706-3711. PMID: 7641180
3. Choi, B.T., et al. 2003. Anticancer Drugs. 14: 845-850. PMID: 14597880
4. Moon, D.O., et al. 2007. Int. Immunopharmacol. 7: 506-514. PMID: 17321474
5. Kung, H.N., et al. 2008. Am. J. Physiol. Cell Physiol. 295: C931-C943. PMID: 17321474
6. Dong, G.Z., et al. 2010. Exp Mol Med. PMID: 20200474
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